Details

Autor(en) / Beteiligte

• Höfler, Denis
• van Gemmeren, Manuel
• Wedemann, Petra
• Kaupmees, Karl
• Leito, Ivo
• Leutzsch, Markus
• Lingnau, Julia B.
• List, Benjamin

Titel

1,1,3,3‐Tetratriflylpropene (TTP): A Strong, Allylic C–H Acid for Brønsted and Lewis Acid Catalysis

Ist Teil von

• Angewandte Chemie International Edition, 2017-01, Vol.56 (5), p.1411-1415

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Tetratrifylpropene (TTP) has been developed as a highly acidic, allylic C–H acid for Brønsted and Lewis acid catalysis. It can readily be obtained in two steps and consistently shows exceptional catalytic activities for Mukaiyama aldol, Hosomi–Sakurai, and Friedel–Crafts acylation reactions. X‐ray analyses of TTP and its salts confirm its designed, allylic structure, in which the negative charge is delocalized over four triflyl groups. NMR experiments, acidity measurements, and theoretical investigations provide further insights to rationalize the remarkable reactivity of TTP. Acid strength by design: Tetratrifylpropene (TTP) has been developed as a highly acidic, allylic C–H acid for Brønsted and Lewis acid catalysis and was tested in Mukaiyama aldol, Hosomi–Sakurai, and Friedel–Crafts acylation reactions. X‐ray analyses, NMR experiments, acidity measurements, and theoretical studies provide further insights to rationalize the remarkable reactivity of TTP.